5-(1H-indol-7-ylamino)-3-((1R,2S)-2-aminocyclohexylamino)-1,2,4-triazine-6-carboxamide

ID: ALA3416026

Cas Number: 1491150-77-6

PubChem CID: 72202597

Product Number: S647457, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H22N8O

Molecular Weight: 366.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1nnc(N[C@@H]2CCCC[C@@H]2N)nc1Nc1cccc2cc[nH]c12

Standard InChI:  InChI=1S/C18H22N8O/c19-11-5-1-2-6-12(11)23-18-24-17(15(16(20)27)25-26-18)22-13-7-3-4-10-8-9-21-14(10)13/h3-4,7-9,11-12,21H,1-2,5-6,19H2,(H2,20,27)(H2,22,23,24,26)/t11-,12+/m0/s1

Standard InChI Key:  FPQNRXITKTZFMF-NWDGAFQWSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    4.9032    5.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682    5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5640    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    5.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    3.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847    2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787    3.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1821    3.0099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1903    1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920    0.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972   -0.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2512   -3.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730   -3.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   -1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    0.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  7  8  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 18  1  0
 26 22  2  0
 16 27  2  0
 27  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416026

   Syk-IN-1

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 366.43

Molecular Weight (Monoisotopic): 366.1917

AlogP: 1.88

#Rotatable Bonds: 5

Polar Surface Area: 147.63

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.34

CX Basic pKa: 9.83

CX LogP: 2.51

CX LogD: 0.11

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -0.80

References

1. Thoma G, Smith AB, van Eis MJ, Vangrevelinghe E, Blanz J, Aichholz R, Littlewood-Evans A, Lee CC, Liu H, Zerwes HG..  (2015)  Discovery and profiling of a selective and efficacious Syk inhibitor.,  58  (4): [PMID:25633741] [10.1021/jm5018863]

2. Thoma G, Veenstra S, Strang R, Blanz J, Vangrevelinghe E, Berghausen J, Lee CC, Zerwes HG..  (2015)  Orally bioavailable Syk inhibitors with activity in a rat PK/PD model.,  25  (20): [PMID:26320624] [10.1016/j.bmcl.2015.08.037]

3.  (2016)  Monocyclic heteroaryl cycloalkyldiamine derivatives, 

4. Cascioferro S, Parrino B, Spanò V, Carbone A, Montalbano A, Barraja P, Diana P, Cirrincione G..  (2017)  An overview on the recent developments of 1,2,4-triazine derivatives as anticancer compounds.,  142  [PMID:28851503] [10.1016/j.ejmech.2017.08.009]

Source

Source(2):

• Scientific Literature
• BindingDB Database